2,2-Dimethyl-1,3-dioxan-5-one → 3-(1-methylindol-3-yl)-4-[3-(2,2-dimethyl-1,3-dioxan-5-ylamino)phenyl]-1H-pyrrole-2,5-dione

HRID 1017577

Reaktionsgleichung

Reaktionsgleichung von HRID 1017577
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:24])[NH:13][C:14](=[O:23])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=2)=[CH:3]1.[CH3:25][C:26]1([CH3:33])[O:31][CH2:30][C:29](=O)[CH2:28][O:27]1.[BH3-]C#N.[Na+]>CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:24])[NH:13][C:14](=[O:23])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][CH:29]3[CH2:30][O:31][C:26]([CH3:33])([CH3:25])[O:27][CH2:28]3)[CH:17]=2)=[CH:3]1

Komponenten

5

Edukt 3

HCID 27331412,2-Dimethyl-1,3-dioxan-5-oneHCID 5003444Sodium cyanoborohydrideHCID 5327711Iron oxide, spent

Produkt 1

HCID 120181673-(1-methylindol-3-yl)-4-[3-(2,2-dimethyl-1,3-dioxan-5-ylamino)phenyl]-1H-pyrrole-2,5-dioneAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 3-(1-methylindol-3-yl)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (200 mg, 0.63 mmol) and 2,2-dimethyl-1,3-dioxane-5-one (98 mg, 0.76 mmol) in MeOH (10 mL) was stirred at room temperature for 15 min., and then NaCNBH3 (79 mg, 1.26 mmol) was added. After stirring the reaction mixture overnight the volatiles were removed under vacuo and the residue was purified by preparatory TLC (1% MeOH/CH2Cl2) to give 3-(1-methylindol-3-yl)-4-[3-(2,2-dimethyl-1,3-dioxan-5-ylamino)phenyl]-1H-pyrrole-2,5-dione (185 mg, 68%). MS(EI): M+ 431, MP: 201-203° C.

Aufarbeitung

  1. stirringAfter stirring the reaction mixture overnight the volatiles
  2. customwere removed under vacuo
  3. customthe residue was purified by preparatory TLC (1% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-9b2e8560d3e44f178d286171522b73fa
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479490B2

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